4-Chloro-3,5-dioxaphosphacyclohepta[2,1-;3,4-']dinaphthalene (BINOL-PCl) as a Bulky and Efficient Reagent for the Transformation of Symmetric and Asymmetric Benzoins to Corresponding Benziles

Subject Areas : Journal of the Iranian Chemical Research

Nader Noroozi Pesyan ¹ , Mahnaz Saraei ² , Bakhshali Massoumi ³ , Maryam Sarbazi ⁴

1 - Department of Chemistry, Faculty of Science, Urmia University, 57159, Urmia, Iran
2 - Department of Chemistry, Tabriz Payam-e-noor University, Tabriz, Iran
3 - Department of Chemistry, Tabriz Payam-e-noor University, Tabriz, Iran
4 - Department of Chemistry, Tabriz Payam-e-noor University, Tabriz, Iran

Received: 2011-01-18 Accepted : 2011-02-28 Published : 2011-03-20

Keywords: 4-Chloro-3, 5-dioxaphosphacyclohepta[2, 1-, 3, 4-']dinaphthalene, Transformation reagent, Benzoin, Benzil,

Abstract :

4-Chloro-3,5-dioxaphosphacyclohepta[2,1-;3,4-']dinaphthalene (BINOL-PCl) was found to be an efficient, bulky and selective reagent for the transformation of symmetric and asymmetric benzoins to the corresponding benziles at 0 °C to room temperature under nitrogen atmosphere in good yield.

References:

[1] R.L. Hudkins, D.L. DeHaven-Hudkins, Bioorg. Med. Chem. Lett. 4 (1994) 2185-2188.
[2] G. Bonde, N.J. Gaikwad, Bioorg. Med. Chem. 12 (2004) 2151-2161.
[3] B. Jiang, X.-H. Gu, Bioorg. Med. Chem. 8 (2000) 363-371.
[4] R.M. Wadkins, J.L. Hyatt, X. Wei, K.J.P. Yoon, M. Wierdl, C.C. Edwards, C.L. Morton, J.C. Obenauer, K. Damodaran, P. Beroza, M.K. Danks, P.M. Potter, J. Med. Chem. 48 (2005) 2906-2915.
[5] B.S. Jursic, D.M. Neumann, K.L. Martin, E.D. Stevens, Org. Lett. 4 (2002) 811-813.
[6] B.I. Ita, O.E. Offiong, Mater. Chem. Phys. 70 (2001) 330-335.
[7] Matsuschita Electric Industrial Co. Ltd. Jpn. Kokai Tokkyo Koho, 8198203, 1981; Chem. Abstr. 1981, 95, 188163v.
[8] L.R. Hillis, R.C. Ronald, J. Org. Chem. 50 (1985) 470-473.
[9] J. March, Advanced Organic Chemistry Reaction Mechanisms, and Structure, John Wiley & Sons, New York, Chapt. 19 (1985)
[10] N. Iranpoor, H. Firouzabadi, M.A. Zolfigol, Bull. Chem. Soc. Jpn. 71 (1998) 905-909.
[11] H. Firouzabadi, A.R. Sardarian, H. Badparva, Bull. Chem. Soc. Jpn. 69 (1996) 685-691.
[12] H.A. Cannon, B.G. Sheldon, K.E. Harding, L.E. Letterman, D.G. Fulton, W.G. Nigh, J. Org. Chem. 38 (1973) 2020-2023.
[13] J. Yamamoto, S. Ito, T. Tsuboi, T. Tsuboi, K. Tsukihara, Bull. Chem. Soc. Jpn. 58 (1985) 470-472.
[14] A. Mckillop, B.P. Swann, M.E. Ford, E.C. Taylor, J. Am. Chem. Soc. 95 (1973) 3641-3645.
[15] B. Tamami, N. Goudarzian, Polymer Bull. 23 (1990) 295-298.
[16] K. Alok, M. Apra De, N. Karchaudhuri, J. Chem. Res (S) (1999) 246-247.
[17] G.S. Hammond, S.W. Chin-hua, J. Am. Chem. Soc. 95 (1973) 8215-8222.
[18] A.R. Hajipour, S.E. Mallakpour, I.M. Baltork, S. Khoee, Chem. Lett. (2000) 120-121.
[19] A.R. Hajipour, I.M. Baltork, Phos. Sulfor and Silicon 164 (2000) 145-151.
[20] I.M. Baltork, A.R. Hajipour, A. Ghahramankhani, Indian J. Chem. Sec. B 39(11) (2000) 863-866.
[21] B. Li, J. Wang, J. Fu, J. Wang, C. Zou, Catal. Commun. 9 (2008) 2000-2002.
[22] S.P. Ivonin, A.V. Lapandin, ARKIVOC viii (2005) 4-9.
[23] N. Noroozi-Pesyan, A.H. Dabbagh, Molecules 10 (2005) 1364-1368.
[24] N. Noroozi-Pesyan, A.H. Dabbagh, J. Iran. Chem. Res. 1(2) (2008) 123-127.
[25] M. Ostermeier, B. Brunner, C. Korff, G. Helmchen, Eur. J. Org. Chem. (2003) 3453-3459.
[26] N. Noroozi-Pesyan, J. Khalafy, H. Khani-Meinagh, Turk. J. Chem. 33 (2009) 527-543.
[27] A. Vogel, Textbook of Practical Organic Chemistry, (VOGEL’S), 4rd Ed., Longman, 1978.
[28] S.K. Kar, A. Kar, J. Org. Chem. 42 (1977) 390-391.
[29] A.H. Dabbagh, N. Noroozi-Pesyan, A.R. Najafi-Chermahini, B.O. Patrick, B.R. James, Can. J. Chem. 85 (2007) 466-474.
[30] F. Toda, K. Tanaka, S. Iwata, J. Org. Chem. 54 (1989) 3007-3009.
[31] S.I. Walter, S.B. Juhannes, Org. React.(N.Y.) 4 (1948) 269-304.
[32] A. Giraud, O. Provot, J.-F. Peyrat, M. Alami, J.-D. Brion, Tetrahedron 62 (2006) 7667-7673.